Isobutyraldehyde → 1-(3,3-Dimethyl-2,3-dihydrobenzofuran-5-yl)-2-methyl-propan-1-ol

HRID 1790210노트

반응식

HRID 1790210 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1.[Li]CCCC.[CH:18](=[O:22])[CH:19]([CH3:21])[CH3:20].[Cl-].[NH4+]>C1COCC1>[CH3:10][C:7]1([CH3:11])[C:6]2[CH:12]=[C:2]([CH:18]([OH:22])[CH:19]([CH3:21])[CH3:20])[CH:3]=[CH:4][C:5]=2[O:9][CH2:8]1

참가 물질

6

반응물 4

HCID 6561IsobutyraldehydeHCID 25517Ammonium ChlorideHCID 53235955-Bromo-3,3-dimethyl-2,3-dihydro-1-benzofuranHCID 178418339Butyllithium

생성물 1

HCID 220414081-(3,3-Dimethyl-2,3-dihydrobenzofuran-5-yl)-2-methyl-propan-1-ol수율 106.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 5-bromo-3,3-dimethyl-2,3-dihydro-benzofuran (2.03 g, 8.93 mmol) in dry THF (10 mL) at −78° C., under argon, was added dropwise n-BuLi (1.6 M in hexane, 13.4 mmol, 8.38 mL). The mixture was stirred for 5 minutes then isobutyraldehyde (1.22 mL, 8.38 mmol) was added and the mixture was slowly warmed up to room temperature and stirred overnight at room temperature. Aqueous ammonium chloride was added and the solution extracted with ethylacetate and the organic extract was dried (Mg2SO4), filtered and evaporated. The residue was purified on silica gel (0% to 20% ethyl acetate in hexane) to give 1.97 g of 1-(3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-2-methyl-propan-1-ol (100%). 1H NMR (300 MHz; CDCl3): δ 0.77 (d, J=6.6 Hz, 3 H), 0.90 (d, J=6.6 Hz, 3 H), 1.33 (s, 6 H), 1.95 (m, 1 H), 4.23 (s, 2 H), 4.28 (d, J=7.2 Hz, 2 H), 6.72 (d, J=8.4 Hz, 1 H), 7.03 (dd, J=8.1 Hz and 1.8 Hz, 1 H), 7.06 (d, J=1.5 Hz, 1 H).

후처리

  1. stirringstirred overnight at room temperature
  2. extractionthe solution extracted with ethylacetate
  3. extractionthe organic extract
  4. dry with materialwas dried (Mg2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified on silica gel (0% to 20% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-8ced0d5f185d429ab03b60c0c8ee990d
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071218B2

반응 노트

불러오는 중…